Looking For Love
by ThePenguinofDeath
Summary: AU Sam/Ruby. If there's one thing that you need to know about the famous fashion journalist Ruby Cortese, it's that she always gets what she wants. And right now, she wants that cute new guy from accounting. One-shot.


**I love this pairing. But for some reason, I've never actually written a Sam/Ruby fic before. However, as I was doing a collection containing jobs that aren't normally included in AU fanfictions (this is the fifth in that 'series'), I decided I may as well include a Sam/ Ruby one. Ruby is a fashion journalist with a reputation, and Sam is the new head of accounting who has no idea what's coming for him. Please review with your comments and criticism so that I know what you think, and I apologise for any OOC-ness – obviously they both have to be quite different here and I'm not sure just how much of their core characterisation I changed.**

**Disclaimer: I don't own Supernatural or any of the characters.**

If there was one thing that you had to know about Ruby Cortese, it was that she always got what she wanted.

When she had one day decided after taking her degree that she wanted to become a fashion journalist, she had applied to every magazine and newspaper in the country until she had managed it. When she had thought that she would make a better Head of the Fashion Department, she had come up with a plan and somehow, within two months, had replaced the sweet lady who had previously held the job. No-one looked to hard into her predecessors sudden resignation – everyone knew that they wouldn't like what they found. And so, when Ruby made it clear that she wanted to date the cute new Head of Accounting, most people agreed that she would find a way to make him hers.

Sam Winchester had no idea what was coming.

On their first proper meeting, Ruby waltzed in with so much confidence that Sam's secretary didn't even check if she had an appointment, walked quickly into Sam's luxury cubicle (the bonus of being a Head of Department) and sat down in the chair opposite his desk before he could even look up.

"Hi! I'm Ruby Cortese, Head of the Fashion Department. I'm not sure we've properly met?"

Sam glanced up with an adorably confused expression on his face, pushing his hair back out of his eyes.

"Um, no... I wasn't expecting to see anyone today. Did you speak to my secretary?"

Ruby ignored his response. "Anyway, the Fashion Department is a little over budget because we had to send two reporters to the Berlin show instead of one – they put up a secondary exhibition which we thought would be worth reviewing. I don't know if you would mind just fixing it for us so that we still have enough money for the Beijing show in two weeks?"

Sam shook his head, sitting back wearily. "I'm sorry, but there really isn't any way that the company can spare any more money at the moment. Our accounts are pressed as it is."

Ruby gave an exaggerated sigh. "But if we don't do our normal spread on Beijing then we'll upset the readers. Some of our readership choose to subscribe to us specifically because we put more emphasis on the Asian shows than other magazines."

"Look, I'm quite busy right now, I don't think I can deal with this today. Could you make an appointment..."

Ruby interrupted Sam by vigorously shaking her head. "Sorry, but I'm going to be really busy for the next week, I'm fully booked. I don't suppose you'd be free to have dinner at some point this week to discuss things? Strictly on work business, or course."

Sam looked wary, but he pulled up a copy of his schedule and glanced over it.

"I can do Thursday night after eight o'clock. But no guarantees that I'll be able to sort anything out for you."

Ruby smiled warmly at Sam. "Wonderful! How does it sound if I make a reservation at the White Hart for eight thirty?"

"The White Hart?" Sam raised his eyebrows at the choice of venue.

"I have expensive tastes."

Sam shrugged. "That sounds fine. Now, I hate to be rude, but I have to finish this in the next three hours."

Ruby nodded. "Of course – I'll leave you to it. It was nice meeting you Mr..."

"Winchester. Sam Winchester."

Of course, Ruby had already known Sam's name, but she didn't necessarily want him to realise that she did.

"Well then, it was nice meeting you Sam."

Sam was already engrossed in his computer again, barely paying attention to the lack of formality.

When Ruby got back to her own cubicle, she silently congratulated herself on arranging a 'dinner date' with Sam on their first meeting. After all, no-one went to the White Hart if they weren't on a date, no matter what excuses Ruby had made.

When Thursday rolled around, Ruby dressed in a sexy yet formal red halter-neck Gucci dress that she had received a few weeks ago, before applying slightly heavier makeup than she would for work. Smiling confidently at herself in the mirror, she picked up the matching clutch and slipped on her patent leather red heels before making her way to the restaurant where she was meeting Sam.

She was pleased to note that he was dressed more formally than usual too – his plain grey work suit had been replaced with a simply cut navy tux that might not be the height of fashion, but certainly showed off his muscular frame more effectively than what he usually wore.

"Hello," She greeted him with a smile, fighting the urge to laugh when his eyes widened slightly and roamed over her body for a second. "I reserved a private room for us so that we wouldn't be disturbed by everyone else's chatter. Shall we?"

Like a true gentleman, Sam held the door open for Ruby and allowed her to lead the way to the dimly lit back room that had been reserved.

A waiter arrived almost immediately, not allowing them any time to chat, and Ruby kept her smile on her face as she gestured to the wine menu.

"Will you join me in having a drink, or do you object to having alcohol while you're working?"

Sam looked conflicted for a moment, seemingly uncomfortable with the whole situation, before replying.

"I'll have the Californian Merlot."

"An excellent choice Sir, if I may say so. And for your partner?"

Ruby didn't give Sam a chance to refute the waiter's statement.

"The Merlot sounds wonderful. We'll have the bottle."

The waiter nodded and left, and Ruby decided to try and make Sam feel a little more comfortable by keeping up the charade that they were here because of work.

"So, have you considered the department's request?"

Sam seemed to settle back into businessman mode, opening up a briefcase that Ruby hadn't noticed and pulling out a couple of complicated looking account statements.

"I looked over the Fashion Department's accounts, but the fact is you already have the third highest budget of any of the departments and I would be hard pressed to allow you any more. I think the bosses would look on it with a disapproving eye, and with money as problematic as it is in the current climate, I can't really afford that."

Ruby sighed. "It's only an extra two hundred dollars or so, nothing that would make a huge dent in finances."

Sam smiled. "Perhaps it doesn't seem that way to someone who wears a $1650 Gucci dress to a work meeting, but believe me, in the grand scheme of things it's a lot more than you would expect."

Ruby raised her eyebrows. "You seem to know a fair amount about fashion. I'm surprised." She found herself very pleased about this development – after all, she wanted a relationship with someone who she could occasionally have a conversation with. The key word there being occasionally.

Sam shrugged, seeming a little embarrassed. "Jess used to talk about it all the time. I guess I picked some of it up. Plus, when I get bored at work I read the companies magazines, and there's always a fashion one lying around."

"Is Jess your girlfriend?" Ruby fought to keep the jealousy out of her voice as she said that – she had been under the impression that Sam was single, if he had a girlfriend this could delay her plan.

Sam sighed, casting his eyes down. "She was. She died, a couple of years ago. House fire. I was away on a business trip, I didn't know until I got back."

Ruby reached across the table and put her hand on Sam's own, squeezing gently and causing him to look up.

"I'm so sorry," She said, injecting sympathy into her voice.

"It was a while ago now."

"Doesn't mean it doesn't hurt."

Sam looked down at where Ruby was holding his hand and Ruby let go, slowly moving her hand back. The way his eyes followed the movement almost like he regretted that she had let go pleased her.

"Have you lost anyone then?" Sam asked after a moment. "Sorry if that's too personal."

Ruby shrugged. "No, it's fine. I lost my parents when I was younger – just a child, really. My dad died when I was four. He wasn't a very nice man, from what I've heard, although I can only remember him as the man who read Winnie-the-Pooh to me before bed. My mum developed depression after he died, battled with it for years before I came home from school one day and discovered her on the floor, stone cold. She had taken an overdose of paracetamol. I went to live with my Uncle after that, but having your parents both die changes things. My cousins never really accepted me either."

The stories that she told were entirely true – although she left a few things out. Like the fact that she helped her mum buy the paracetamol because she believed her mum was going to a better place. And the fact that her cousins had teased her until she worked out that the best way to shut them up was revenge. Ruby was very good at enacting revenge, she had had plenty of practise over the thirty odd years of her life.

Sam looked at Ruby with an expression of absolute understanding, taking her hand again – although he didn't seem to realise that he had done it.

"My mum died when I was a child too. Six months. I don't even remember her. My brother does, Dean, and he never coped very well with it. Both him and dad were so sad all of the time that I had to run away when I was sixteen. I needed some happiness in my life. They've never forgiven me."

Ruby moved her other hand to clasp Sam's between her own.

"It's not your fault." She said simply.

"It feels like it is sometimes."

Anything else that they had to say was interrupted by the arrival of the waiter with the wine and a basket of bread.

"Have you decided what you want to order?"

Sam looked like he'd forgotten entirely that they were in a restaurant and hurriedly picked up the menu, so Ruby turned a charming smile on the waiter.

"I'll start with the traditional vegetable salad, followed by the roast lamb please. Without gravy."

The waiter quickly made a note of her order before turning to Sam, who hurriedly closed the menu.

"I'll also start with the salad, but for main course I'll have the beef in speciality sauce."

The waiter left, and Sam seemed to become himself again, almost shaking off the events of the past few minutes. He had pulled his hand back with the arrival of the waiter.

"Sorry about that, I don't know what came over me." He commented.

Ruby shrugged. "It's fine – sometimes you just need to talk about these things. It was nice, for me, being able to discuss it without being smothered in pity." She held up the bottle of Merlot. "Wine?"

Sam nodded gratefully and Ruby poured him a full glass, before carefully pouring one for herself.

"Back to business, I'm really not sure that the company can spare the money. It just isn't viable. Is there absolutely no way that you can save $200 anywhere else?"

Sam seemed concerned, and Ruby hid a smile at the fact that he was now emotionally invested. This was going better than she had hoped.

She sighed. "Not really, not without sacrificing the quality of our articles. The only real way to save would be to only send two reporters to Beijing, but that's a big show and two people couldn't see everything there is to see. We'd probably miss the scoop on something big and that then leads to people thinking we're going downhill and cancelling subscriptions. Plus, the employees get paid per show and they'll be annoyed if they don't get as many opportunities as normal."

"If I could help you out, I would, but even though I run accounting it's not really my decision." Sam was clearly conflicted.

"It's OK, I understand. Well, I don't really understand money stuff, but I understand that it's hard for you to help. I'll talk to the boss about it tomorrow and see if he can be persuaded." Ruby had no doubts that she could persuade him – usually she would have gone to the boss directly, as Zachariah would always do her favours, but going to Sam provided a perfectly believable excuse for her to spend time with him.

"I doubt he'll change his mind, he seems quite strict to me." Sam warned.

Ruby laughed, taking a sip of wine. "He is. You don't want to know some of the nicknames people've come up with over the years."

Sam looked intrigued, but before he could say anything their salads arrived and conversation stopped so they could eat.

The rest of the meal passed quickly, the two making casual conversation and getting closer and closer throughout the evening. Ruby found herself thrilled at how well everything was going, and also surprised in a way about how much she liked Sam – he had been a conquest, someone to chase after, but he was also very interesting and the amount she liked him as a friend was an unexpected bonus.

When it got to the end, Sam held his arm out for Ruby like a date would and she found herself giving a true smile rather than a fake one as she took it and allowed him to lead her out of the restaurant.

"You know, I had fun tonight." Sam commented shyly as they walked out. "We should do this again. Not as a work thing, as a friend thing."

Ruby paused, turning so that she was standing facing him, only a few centimetres away.

"Just as friends?" She asked, her voice layered with promises of something more.

Sam hesitated for a moment, almost like he was considering something, before muttering, "Screw it," and leaning in to capture Ruby's lips.

It wasn't like a first kiss. Ruby kissed back with enough passion to set an ocean liner on fire, and Sam responded by wrapping his arms around her and pulling her off her feet (despite the fact that she was wearing six-inch heels) so that he could more effectively attack her mouth with his own. They both entirely forgot that they were in front of one of the most upmarket restaurants in the area until Ruby's taxi pulled up and the driver coughed to break them apart.

"My place?" Ruby asked, although she wasn't exactly intending to take no for an answer.

"God yes." Sam replied, his voice sounding wrecked.

When they arrived at work the next morning together, Ruby sporting a red love bite on her neck and Sam sitting down awkwardly at his desk to avoid putting pressure on the claw marks down his back, no-one was surprised. After all, Ruby Cortese always got what she wanted.

Their marriage a year later didn't come as much of a shock either.

**I hope you enjoyed this as much as I enjoyed writing it! Please do leave a review with all your comments, reviews keep me going. Feel free to PM me with any requests for pairings you want me to add to this collection and any jobs you want them to hold!**

**Previous fanfictions in this collection:**

**Work (Destiel, Supernatural)**

**Code To My Heart (Destiel, Supernatural)**

**GINASFS (Sabriel, Supernatural)**

**Anything Can Happen (Sabriel, Supernatural)**


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